Ether lactone

ABSTRACT

The invention relates to the ether lactone of formula (I) which is characterized by interesting and original odor characteristics, which diffuses extremely well and is suitable for use as a fragrance, for example in cosmetic preparations, technical products or in alcoholic perfumery.

FIELD OF THE INVENTION

The present invention relates to an ether lactone of a specificstructure and its use as a fragrance.

PRIOR ART

Many natural fragrances, relative to their demand, are available incompletely insufficient quantities. For example, 5,000 kg of rose petalsare needed to produce 1 kg of rose oil. The consequences include agreatly limited annual production worldwide and a high price. It istherefore apparent that the fragrance industry has a constant need fornew fragrances that exhibit interesting scents. On the one hand, therange of naturally available fragrances can be supplemented thereby, onthe other hand it is thus possible to make the necessary adaptations tothe ever-changing fashion in taste. Furthermore, this makes it possibleto meet the ever-increasing demand for scent enhancers for products ofdaily use, such as cosmetics and cleaning agents.

Moreover, there is generally a constant demand for synthetic fragrancesthat can be produced inexpensively and with a uniform high quality, andwhich have the original olfactory characteristics. In particular, theyare intended to exhibit pleasant, sufficiently intense scent profilesthat are as natural as possible and are novel in terms of their quality.Such synthetic fragrances are also intended to be capable ofbeneficially influencing the scent of cosmetics and goods of daily use.In other words, there is a constant demand for compounds that exhibitcharacteristic novel scent profiles while simultaneously ensuringconsiderable staying power, intensity of scent and strong diffusion.

Perf. Essent. Oil Rec. 1967, 58(9), pages 648-650, in FIG. 1 on page648, column 5, line 5 of the table, lists an ether lactone that exhibitsan “average” musky scent and which is described in more detail by way ofa formula.

DESCRIPTION OF THE INVENTION

It was found that the ether lactone of general formula (I) superlativelymeets the aforementioned requirements in every way and that it can beadvantageously used as a fragrance exhibiting diverse nuanced scentsthat in turn offer good staying power.

The subject matter of the present invention is, initially, the etherlactone of general structure (I)

The invention further relates to the use as a fragrance of the etherlactone of general structure (I) described above in detail.

Compound (I) is characterized by an odour characteristic in which amusky quality dominates. Apart from an intense musky quality, scentaspects stand out that can be described as sweetish, redolent of balsam,with waxy qualities. (I) has excellent stability in formulations forcosmetics and perfumes of daily use.

Compound (I) may be produced on the basis of synthesizing techniquesknown in organic chemistry.

In perfume compositions, compound (I) enhances harmony and emanation aswell as naturalness and staying power. Dosage is tailored to whicheverscent is being striven for, while taking the composition's otherconstituents into account.

It was not foreseeable that compound (I) would exhibit theaforementioned scents, which provides further confirmation of thegeneral experience that the olfactory characteristics of knownfragrances do not permit automatic conclusions regarding the propertiesof structurally related compounds, since neither the mechanism of scentperception nor the effect of the chemical structure on scent perceptionhave been adequately researched and since it therefore cannot normallybe predicted as to whether a modified structure of known perfumesactually causes the olfactory characteristics to be modified or as towhether these modifications are assessed positively or negatively by theperson skilled in the art.

Attention must be explicitly drawn to the fact that the scentcharacteristic of compound (I) according to the invention differsclearly from the ether lactone that exhibits merely an “average” muskyscent and which is described in more detail by way of a formula in Perf.Essent. Oil Rec. 1967, 58(9), pages 648-650, in FIG. 1 on page 648,column 5, line 5 of the table. As far as the person skilled in the artwas concerned, it was therefore neither foreseeable nor evident—on thebasis of the structure mentioned in Perfum. Essent. Oil Rec. 1967,58(9), pages 648-650, in FIG. 1 on page 648, column 5, line 5, and as aresult of the introduction of a methyl substituent at an entirelyspecific position—to arrive at a compound that exhibits a much moreintense musk scent with additional further scent qualities.

Owing to its scent profile, the formula (I) compound is, furthermore,particularly suitable for modifying and enhancing known compositions.Particular emphasis should be placed on its outstanding intensity ofscent, which contributes, in a quite general way, toward thecomposition's refinement.

The formula (I) compound can be combined with numerous known fragranceingredients, such as other perfumes of a natural, synthetic or partiallysynthetic origin, essential oils and plant extracts. The range ofnatural fragrances may include components that are both readily volatileas well as ones that exhibit medium and low volatility. The range ofsynthetic fragrances may include representatives of virtually anysubstance class.

Examples of suitable substances with which compound (I) can be combinedinclude in particular:

-   (a) Natural products such as evemia furfuraceae (tree moss)    absolute, basilicum oil, citrus oils such as bergamot oil, mandarin    oil, etc., mastic absolute, myrtle oil, palmarosa oil, patchouli    oil, petit grain oil, absinth oil, myrrh oil, olibanum oil, cedar    wood oil, sandal wood oil, East Indian, guajak wood oil, cabreuva,-   (b) Alcohols such as famesol, geraniol, citronellol, linalool,    nerol, phenylethyl alcohol, rhodinol, cinnamyl alcohol, Sandalore    [3-methyl-5-(2.2.3-trimethylcyclopent-3-en-1-yl)pentan-2-ol],    Sandela [3-isocamphyl-(5)-cyclohexanol], Mugetanol,-   (c) Aldehydes such as citral, Helional®, alpha-hexylcinnamaldehyde,    hydroxycitronellal, Lilial®    [p-tert.-butyl-α-methyldihydrocinnamaldehyde],    methylnonylacetaldehyde,-   (d) Ketones such as allyl ionone, α-ionone, β-ionone, Isoraldein,    methyl ionone, noot katone, Calone, α-, β- and γ-irones, damascone,-   (e) Esters such as allyl phenoxyacetate, benzylsalicylate,    cinnamylpropionate, citronellyll acetate, decylacetate,    dimethylbenzylcarbinylacetate, ethylacetoacetate,    hexenylisobutyrate, linalylacetate, methyldihydrojasmonate,    vetiverylacetate, cyclohexylsalicylate, isobornylisobutyrate,    evernyl,-   (f) Lactones such as gamma-undecalactone,    1-oxaspiro[4.4]nonan-2-one, cylopentadecanolide, ethylene    brassylate,-   (g) Ethers such as Herbavert, ambroxan,    as well as various further components often used in the perfume    industry such as musk and sandal wood fragrances, indole,    p-menthane-8-thiol-3-one, methyleugenol and methylanthranilate.

Noteworthy is, furthermore, how the structure (I) compound rounds offthe scents of a wide range of known compositions and harmonizes thesewithout, however, being dominant in an unpleasant manner.

The usable proportions of compound (I) in fragrance compositions rangefrom approximately 1-70% by weight, based on the entire mixture.Compound (I) and fragrance compositions that contain compound (I) can beused both to perfume cosmetic preparations, such as lotions, creams,shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwashand deodorants, as well as in alcoholic perfumery (e.g. eau de cologne,eau de toilette, extracts). There is also the possibility to use theaforementioned to perfume technical products such as detergents andcleaning agents, fabric softeners and textile treating agents. Toperfume these various products, the compositions are added thereto in anamount effective olfactorily, in particular in a concentration of 0.01to 2% by weight, based on the entire product. These values do not,however, constitute limits since the experienced perfumer can stillattain effects with even lesser concentrations or can construct novelcomplexes with even higher dosages.

EXAMPLES Example 1

90 g (1 mol) 2-methylpropane-1,3-diol and 27 g (0.5 mol) sodiummethylate were suspended in 200 ml xylene and heated to refluxtemperature in a water trap at 140° C. for 24 hours while being stirredvigorously. Then, 99 g (0.35 mol) methyl 11-bromoundecanoate wascontinuously added dropwise to the mixture over approx. 3 hours at 140°C. and refluxed for another 3 hours. Afterward, the gas chromatogramstill showed approx. 25-% unconverted methyl bromoundecanoate. 90 gsodium methylate (30% in methanol) and 10 g polyethylene glycol 600 wereadded and heated for another 4 hours at 132° C. in the water trap,whereby methanol was removed by distillation.Further Processing:

The reaction mixture was concentrated, the 80 g crude product thusobtained was slowly distilled over on a bulb tube distiller. 20 g 30-%product and 20.2 g 75-% material were trapped as fractions.

Analysis:

The IR spectrum (ATR technique) showed characteristic bands at 1112,1174, 1248, 1733 cm⁻¹ and a vibrational CH range from 2858 to 2929 cm⁻¹.

The ¹H-NMR spectrum (400 MHz in CDCl₃) showed 1 methyl group (2singlets, 3H) at 0.95 ppm. A signal peak at 1.3 ppm corresponds to 5 CH₂groups, 2 broad signals at 1.6 and 1.7 ppm correspond to 3 CH₂ groups,and one signal at 2.3 ppm corresponds to 1 CH₂ group. The signal at 2.0ppm is assigned to the CH at which the methyl group is positioned. Asignal mixture that had been split up in a complex fashion was locatedin the range from 3.3. to 4.2 ppm; this corresponds to 3 CH₂ groups inthe vicinity of the oxygen atoms in the ring.

Scent Characteristic:

When first smelled, typically musk, sweetish, redolent of balsam, withwaxy qualities and ones such as a hot domestic iron; after 24 hours onthe scent strip, the subsequent smell was redolent of musk, warm wax;this scent remained for several weeks.

1. An ether lactone of general structure (I)


2. A use of said ether lactone of general structure (I)

as a fragrance.
 3. Fragrance compositions having a content of said etherlactone (I)

said compound (I) being present in an amount of 1 to 70% by weight,based on the entire composition.